Ethanol → tert-Butyl {[1-(ethoxymethyl)piperidin-4-yl]methyl}carbamate

HRID 736407Notes

Reaction equation

HRID 736407 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.C=O.[C:18](=[O:21])([O-])[O-].[K+].[K+].[CH2:24](O)[CH3:25]>>[CH2:24]([O:21][CH2:18][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3][CH2:2]1)[CH3:25]

Participants

5

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 67233964tert-Butyl {[1-(ethoxymethyl)piperidin-4-yl]methyl}carbamate

Procedure

To a stirred solution of tert-butyl (piperidin-4-ylmethyl)carbamate (7.0 g, 33 mmol) in ethanol (19 mL), paraformaldehyde (1.2 g, 39 mmol) and potassium carbonate (5.4 g, 39 mmol) were added at ambient temperature. The mixture was stirred at ambient temperature for 4 h. The mixture was filtered and the filter cake was washed with ethanol (50 mL). The volatile components were removed by evaporation to give the title compound 8.9 g (quant.) as a white powder.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with ethanol (50 mL)
  3. customThe volatile components were removed by evaporation

Sources & evidence

ORD record
ord-098c7e94a5f94565bd7d3dcd96ea36f6
Source dataset
uspto-grants-2009_09
Patent number
US07595329B2

Reaction notes

Loading…